Jeremy Gilbert, PIMP
by Doctor Sexy
Summary: Jeremy Gilbert is a pimp, with first class hookers Bonnie, Caroline and his highest price hooker, Damon. Fairly cracky, partially an excuse to have every character have sex with every other character. Enjoy some main pairings are Klefan and Deremy, but pretty much everyone's going to get together. Please submit pairings you want!
1. Delena

Elena woke up one morning and walked downstairs to see her brother Jeremy decked out in all pink, except his gator shoes, those were green. He carried a pimp cane with him with a lion's head at the top.

"Well, you're dressed up today," Elena said. "What's the occasion?"

Jeremy handed her a small business card that read: _Jeremy Gilbert. P.I.M.P. 555-6667._

"Wow," Elena said. "So you're in the business now? Who do you have as prostitutes?"

"Well, so far, I only have three," Jeremy said. "But they really are of the highest caliber. Bonnie Bennett, Caroline Forbes, and Damon Salvatore."

"I want in!" Elena said a little too enthusiastically.

"You want to be a hooker? You're the best sister ever!" Jeremy said.

"No, I want to be a customer," Elena said. "I want Damon."

"Sweet, he's a bit pricey. A hundred bucks for every inch of his penis. But I'll let you measure," Jeremy said.

"Do I measure hard or soft?" Elena asked.

"Hard," Jeremy said. "Damon's a grower not a shower."

"Okay, I'm in," Elena said. "Where is he?"

"At my whorehouse," Jeremy said. "I'll take you there."

The whorehouse turned out to be the Salvatore home. Damon answered the door, wearing nothing but leather pants. "Hello, Jeremy. Have you brought me a customer?"

"I DID NOT AGREE TO MAKE OUR HOUSE A WHOREHOUSE!" Stefan yelled down at Damon.

"Doesn't matter," Damon said. "You're just jealous that Jeremy didn't want you."

"I am not!" Stefan said and he went to go brood in his room.

"Alright, drop trou," Jeremy said.

"Already?" Damon asked. "I don't need to be asked twice." He pulled down his leather pants with some difficulty.

Jeremy pulled out some measuring tape. "How do you make this thing work?" he said poking Damon in the penis.

Elena dropped to her knees and took Damon into her mouth. The results were immediate. Then she got up and then she took the tape and measured.

"Ten inches," Elena said. "Well, it'll have to do."

"That'll be a thousand bucks, and then you've got him for the hour," Jeremy said.

Then Elena went in her purse and counted out a thousand ones. Jeremy groaned. "What? Stripping pays the bills."

* * *

Soon Elena was alone with Damon in Damon's room. Damon pants were still pulled halfway down. Elena stripped them off. "Now where shall we start?" Elena said, licking her lips.

"Well, I was thinking we'd start off with a bit of foreplay in my downtown area," he said motioning at his crotch. "And then we'd do it doggie style."

"No, Damon," Elena said. "I wasn't serious. I paid a thousand bucks. You don't get an opinion."

"Alright, then. Lie down, let's get this over with," Damon said, but his expression gave away that he was enjoying himself.

"You don't get to be on top Damon!" Elena said.

"But that's not fair!" Damon whined.

"No uterus, no opinion!" Elena yelled. "Now get on the bed." Damon laid face down on the bed. "The other way, dickhead!"

Elena stripped in slow motion while Damon waited impatiently on the bed. Then Elena went in her purse and grabbed a whip. "Now you listen to everything I say," Elena said.

"Yes, ma'am," Damon said.

"I didn't say you could talk!" Elena said whipping him right in his juicy thigh.

"Ahh!" Damon screamed.

"Quiet, bitch!" Elena said. Then she mounted his man pole and rode him like a wild animal.

Damon groaned. Elena whipped his a good one in the chest. "Get up!"

"Okay, okay!" Damon said standing up. He was rewarded with a swift whip in the ass. "Isn't this supposed to be fun?"

"I'm having lots of fun!" Elena said pushing Damon up against the wall. "Bend your knees!" Damon did as he was told. Elena grabbed Damon's dick and put it inside her. Then she started humping him hard.

Elena pulled Damon's hair hard. "Oh, yeah," she said. Then she got down and laid on the bed. "You want to be on top?"

He quickly obliged and entered her. She clawed at his back hard enough to make it bleed. Then she came with a loud yell.

Then she pulled away and got up. "Okay. Have a nice day," she said.

"But wait! That's not fair!" Damon protested.

"I got what I paid for," Elena said and she slammed the door.

* * *

**A/N: Thanks for reading! Be sure to review and tell me what you think. Also feel free to suggest to me any pairings. I'll probably take all of them. Unless you want me to write a sex scene with Tyler because that is just not happening. Prepare for some Team Salvatore in the future.**


	2. Klefan

Stefan was really mad at Damon and Jeremy for turning the Salvatore home into a whorehouse. He sat in his room brooding and reading Shakespeare or something else equally boring and gay. He heard angry yells from Elena and scared yells from Damon. Stefan groaned and grabbed a phone, dialing Klaus's number.

"Klaus," Stefan whined. "Jeremy and Damon turned our house into a whorehouse."

Klaus sighed. "I just really don't care, Stefan."

"Help me get back at Damon," Stefan said.

Then Klaus had an excellent idea. "Is Damon turning tricks now?"

"Yes," Stefan said exasperatedly.

"So all you have to do is buy him and get your revenge," Klaus says.

"I don't think revenge sex is really going to help this situation," Stefan mused.

"No," Klaus said excitedly. "You make him cross dress in public. With a pink feather boa and some nice fishnets. Oh, and let me know when you're going to do this, because I need to be there to see it."

"That's a great idea!" Stefan said. "I love you, Klaus!" He hung up. Then he phoned again deciding to add, "Just as friends." Which made Klaus cry hysterically for seven hours.

Stefan ran into Damon's room to find Damon jacking off. Damon didn't stop but just groaned upon Stefan's arrival. "What do you want?"

"I came to you know, buy your services," Stefan said.

"Well will you at least be a decent client and let me finish?" Damon asks.

"We're not going to have sex!" Stefan said, slapping Damon in the back of the head, which prompted Damon to ejaculate into his own hand.

Damon called Jeremy. "Yeah, Jer. I have another client. Who wants to buy me and not have sex with me? Yeah I don't get it either."

It took just a minute for Jeremy to show up, almost as if he had been outside Damon's door waiting. Mostly because that's exactly what he had been doing.

"Stefan, good to see you. Have you thought more about hooking for me?"

"No, I haven't," Stefan said bemused. "I'm just here to buy Damon. For like three hours."

"Three hours?" Jeremy said. "I also have a side business of selling viagra, which I suggest you both could use if you're going to go at it that long."

"That won't be necessary. Just the three hours. How much?" Stefan asked.

"Fifty thousand dollars," Jeremy said, pulling a random number out of his ass.

"Can I write you a check?" Stefan asked. Jeremy nodded and Stefan wrote the check.

Jeremy pulled a bottle of scotch out of nowhere. "Why don't you two help yourself to scotch since you're both such good business partners?"

Stefan nodded and he poured himself and Damon both a glass which they chugged back quickly.

"Okay, so here's what you're going to do," Stefan said. "I just have to call Elena first." He pulled his phone out of his pocket and dialed her number. "Elena, I need to borrow a pink feather boa, a halter top, fishnets, and hooker boots. Thanks for understanding."

In ten short minutes Elena was over with the goodies. "Put them on Damon," Stefan said.

Damon went to walk to the washroom to change but Elena glared at him. "Get dressed here."

"You already got what you paid for remember?" Damon yelled.

"Do it," Stefan commanded. Surprisingly, the attire fit Damon perfectly, other than being ridiculously slutty. "Okay, now we're going to the grill." He quickly sent a mass text to everyone he knew to meet at the Mystic Grill immediately.

* * *

By the time he got to the grill, Stefan realized he had an erection._ What the hell_? he thought. _Jeremy must have spiked the scotch with Viagra. That little bastard._

Sure enough, Stefan looked over at Damon and could see Damon's little soldier standing at attention, pushing on his leather skirt.

Bonnie walked over laughing. "What the hell?" She was dressed in a cardigan and horn-rimmed glasses on Jeremy's advice that she'd be a sexy librarian.

"You're just jealous that I'm getting all the action," Damon said stubbornly. "Has anyone bought you yet?"

"Not yet..." Bonnie said quietly.

"Exactly," Damon said proudly.

"I'm sure someone will buy you," Elena said patting Bonnie's hand and winking.

Alaric walked into the bar. He immediately did a double take. "What it God's name?"

Stefan smiled. "Damon's trying a new look."

"It suits you," Alaric said.

"I'm a prostitute now," Damon said proudly. "And Stefan bought my services because he's a creepy perv."

"Is he telling the truth?" Alaric said disgustedly. Elena nodded. "Stefan that's disgusting! What's wrong with you? And do you have an erection?"

"Eww, incest is gross," Elena said to Alaric. Then she whispered into Stefan's ear. "Don't worry I think it's kind of hot."

"Where's Klaus?" Stefan said angrily. "This whole thing was his idea." He phoned Klaus. "Why aren't you at the grill?"

Klaus was still crying and he said something Stefan couldn't understand.

"So umm. I'll talk to you tomorrow when you calm down, okay?" Stefan said.

Liz Forbes walked into the grill. Her eyes lit up. "Damon, how wonderful that you came out of the closet finally!"

"Wait... I didn't..." Damon started.

"This is actually wonderful," Liz said. "I'm actually a man, so we can date now!"

"Actually, no thank you," Damon said politely because he was scared of her.

"I have to go find Klaus," Stefan said. "You're off the hook, Damon."

"But I like dressing like this!" Damon yelled, but Stefan was already gone.

* * *

Stefan knocked on Klaus's door. Klaus opened the door, still crying.

"What is your issue?" Stefan asked.

"I don't want to be friends," Klaus whined.

"Fine, let's just have sex and get it over with," Stefan said.

"Really?" Klaus said, immediately stopping crying.

"Sure, why not?" Stefan said. He already had an erection so he didn't see it being a problem.

Klaus led Stefan to the bedroom by the hand. Stefan stripped his shirt off, and Klaus smiled approvingly. Klaus quickly removed all of his clothing then reached for the zipper of Stefan's jeans. He slowly pulled the jeans down, enjoying the slow torture.

Then they did the do, Stefan top and Klaus bottom.

"Wow, that was actually pretty decent," Stefan said afterwards. "I have to call Jeremy."

He pulled his phone out a called Jeremy. "Jeremy the Viagra you spiked my drink with was amazing. I'd like to buy some more."

"Umm... I didn't spike your drink with Viagra, dude, you're just aroused. Probably by Damon's sexy outfit," Jeremy said.

"Fuck," Stefan said.

* * *

**A/N: I'm sorry there wasn't much sex in this chapter. The next chapter will be a surprise pairing or threesome so stay tuned. :) Oh and review?**


	3. Beremy and Klefan

So anyway, Stefan returned to the Salvatore whorehouse and entered his room to find Jeremy had set up on office in there.

"Can I help you?" Jeremy asked. He was looking classy in a high price suit.

"You're a pimp, what the hell do you need an office for?" Stefan asked.

"Paperwork," Jeremy said.

"You're running an illegal prostitution organization," Stefan said. "You're not supposed to have paperwork!"

"I'll be done with your room eventually," Jeremy said. Stefan ran out of Jeremy's office/his bedroom grabbing a book and decided to angstily read on the couch.

* * *

Jeremy was busy doing paperwork which consisted of drawing Alaric and Damon having sex on a unicorn. Bonnie knocked on Jeremy's office door. Jeremy opened up and hugged her tightly. "Bonnie, my first class hooker!"

"I don't feel very first class," Bonnie said. "No one has bought me yet."

"Well come to Papa," Jeremy said. "I just came by 50 thou I'm sure I could spare some change."

"Really?" Bonnie said, looking up at him like a kid on Christmas.

"Of course," Jeremy said. "You're a fine ass bitch and I'm a straight up G. We should get it on."

"Oh, Jeremy, I thought you'd never ask!" Bonnie said running into his arms.

* * *

Stefan decided that Jeremy had to be done using his office. How much paperwork could he have? He opened the door to find Jeremy and Bonnie in a comprising position, AKA Bonnie had her feet behind her ears and Jeremy was riding her like a pony. Neither of them seemed to notice that Stefan had come in. Jeremy stopped. "It's just not coming to me," he said.

Stefan angrily slammed the door shut. _Fine, I'll just sleep on the couch_, he thought.

Unfortunately, he could hear loud yelling from Damon's room. Was that Caroline's mom yelling, "Oh yes, Damon that's just the spot!"

"Caroline's mom! You're so experienced!" Damon yelled.

"God, don't do that, you have better moves than that!" Liz yelled back.

Jeremy ran into the room. He wasn't going to let Liz get away without paying. "Damon! You know you're supposed to consult me on any deals you make!"

"Relax, we're just playing chess," Damon said.

"It costs extra if you don't want to have sex," Jeremy informed Liz.

"Well..." Liz said, biting her lip. "I can give you a couple grand, will that do?"

"You sicken me," Jeremy said. "Get out of here."

Liz ran away crying.

Meanwhile Stefan decided he couldn't live in a whorehouse where everyone was having loud sex, so he went to Klaus's house.

"Stefan!" Klaus said enthusiastically. "Come in."

"I just need somewhere to sleep," Stefan said.

"Well, I don't have any guest bedding... So you're going to have to sleep in my bed," Klaus said.

"Could this day get any worse?" Stefan cried out loud.

Apparently it could because Klaus ended up cuddling him in a death grip once they got into bed. "Your hair smells good," Klaus murmured.

Eventually, Klaus fell asleep, but that was no better. He was tossing and turning. He kicked Stefan in the junk. Then he punched Stefan in the face. Stefan tried to get out of bed and go back to his own house, but Klaus pinned him down to the bed.

* * *

**A/N: Sorry this chapter is so short, but I plan to update again tomorrow. This chapter was per request of Bonnie/Jeremy, but later there will be Bonnie/Jeremy/Tyler. Also I'm going to try to fit in Stefan/Caroline. And many more pairings to be had.**

**This chapter is dedicated to the memory of my sister's favorite pants.**


	4. Klamon

Damon finally decided to change out of his fishnets and miniskirt, into just his leather pants and nothing else. "Jeremy, I really don't think we need to charge people to play chess with me."

"Are you the brains of the business or are you the hot ass, Damon?" Jeremy asked.

"But-"

"Answer me, Damon. Are you the brains or are you the hot ass?" Jeremy asked again.

"I'm the hot ass," Damon replied.

"Good, now I have to go see Bonnie in the bedroom, if you know what I mean," Jeremy said.

"You're doing Bonnie?" Damon asked disappointedly. "I thought I was your favorite whore."

"Of course you are," Jeremy said, stroking Damon's hair. I'm not going to mention if it was his hair above or below his waist. "It's a pity lay because no one has bothered to buy her."

"Not like I wanted to sleep with you," Damon muttered.

"Good," Jeremy said. "We can't have you worn out for our customers, now can we?"

"No, sir," Damon said.

"Atta boy," Jeremy said, slapping him in the ass. "Go get 'em Big D."

* * *

Klaus woke up in Stefan's arms. "What the hell is this?"

Stefan groggily opened his eyes. "What's going on?"

"You're cuddling. Why are you cuddling?" Klaus asked.

"You're the one who's in love with me!" Stefan said defensively.

"I'm not in love with you!" Klaus said. "It was a one night stand, seriously Stefan could you be any more clingy?"

"But you said... you didn't have any guest bedding so I'd have to sleep in your bed. That's a fucking line," Stefan said.

"No, it's not. The bedding is out at the drycleaner's," Klaus said.

"You said my hair smelt nice!" Stefan protested.

"Well it smelled like coconut!" Klaus said.

"Well... I guess I did try a new shampoo..." Stefan muttered.

"Get out of here," Klaus said. "I don't want to start a relationship with you."

"Fine," Stefan said, feeling oddly sad.

* * *

Three hours later, Klaus realized he was just being a bitch and he actually did want to start a relationship with Stefan. He called Stefan.

"What Klaus?" Stefan said angrily.

"I want you back," Klaus said.

"We were never together," Stefan pointed out.

"Are you saying no?" Klaus asked.

"I'm saying no," Stefan said. "You were a real ass today, I don't think I need that in my life."

So Klaus did what any self-respecting man would do and went to go buy the love of his life's brother for some sad sex.

He knocked on the Salvatore door. Jeremy answered. "Klaus, good to see you. Although, I'm sorry to tell you I still haven't convinced Stefan to become a dollar whore yet."

"I'm here for Damon," Klaus said.

Jeremy's eye's lit up. "Alright, but he's our most expensive prostitute. $20, 000 for an hour."

"Fine, where is he?" Klaus growled.

Damon was still attempting to put on his leather pants. Klaus ripped the pants right off of Damon. "You won't be needing these."

"Have you paid Jeremy?" Damon asked, afraid Jeremy would beat him if he didn't.

"Yes," Klaus said, throwing Damon against the wall.

"Okay then," Damon said, somewhat nervous at all of Klaus's anger. Then he realized Klaus wasn't just angry he was actually crying. "Why are you crying?"

"Shut up! I didn't pay you to talk!" Klaus said, undoing his belt and his zipper. Then he slowly unbuttoned his shirt.

"Strip faster!" Damon complained.

Klaus slapped Damon across the face before removing the rest of his clothes. "Lay down on the bed." Damon laid down on his back. "The other way, dickhead!"

"Fine!" Damon said, laying on his stomach.

Klaus laid on top and entered Damon.

"Can't you at least use some lube?" Damon whined.

"NO!" Klaus said, punching Damon in the back of the head and sobbing. "Stop talking, Stefan!"

"I'm not Stefan you psychopath!" Damon cried.

Klaus gripped Damon's hips and bore into him hard. He thrusted deeply, and Damon tried not to cry out in discomfort, as Klaus called out Stefan's name over and over again through sobs.

Finally, Klaus finished with a loud scream. Jeremy walked in. "You went one minute over your hour. I need another 20K."

"Are you fucking serious?" Klaus asked, throwing Damon across the room and through the wall.

Jeremy ran to Damon's aid. "Damon, are you hurt?"

"I'm fine," Damon said uncertainly.

Jeremy tenderly kissed Damon on the forehead before turning his attention back to Klaus. "And you ripped his pants! Those are custom made! Twenty-one thousand dollars you owe me."

"Fine!" Klaus said writing a check and going home to cry some more.


	5. Beremyler and Steroline

Jeremy was wearing the pimpingest clothes ever, except for his rubber boots with little rubber ducks on them because it was raining out. He was walking his bitches to class, Caroline on one arm wearing a skanky dress, and Bonnie on the other arm wearing the exact outfit Stefan paid Damon to crossdress in.

Stefan walked up to Jeremy. "Jeremy this is important," he said. "I need to make Klaus jealous."

"Well I have just the two fine ladies for you!" Jeremy said. "Have your pick. Caroline's better in bed, but Bonnie's vagina is prettier."

"Umm... I'm going to have to go with Caroline," Stefan said.

"Excellent, that'll be four shillings," Jeremy said.

"So that's like four cows, right?" Stefan said.

"I'll Google it," Jeremy said pulling out his phone. It took awhile for the internet to load. "That would be five cents US."

Caroline forced a smile, wanting to be the best hooker she could be.

"That's all?" Stefan said, handing Jeremy a nickel.

"So where are we going to do it?" Stefan asked, using his best pick up line.

"Oh, I know all the best places. The janitor's closet, the girl's bathroom, the men's bathroom, the detention room..."

"Yeah, that sounds good, let's do that one," Stefan said.

"Okay, then we've got to get detention first," Caroline said slyly.

Tyler walked up. Caroline had just broken up with him in favour of becoming a hooker. He was determined to get back at her. He looked awkwardly away from Caroline, who was giving him a death glare. "Jeremy I want to buy you," Tyler said.

"I don't think you understand how this works," Jeremy said. "I'm the pimp. You don't buy the pimp, you buy the hooker." He motioned at Bonnie's chestal region.

"I've got... ten thousand," Tyler said.

"Well, okay..." Jeremy said. Then he whispered loud enough for Bonnie to hear. "But you have to buy Bonnie too. I'm feeling bad for her. I mean honestly no one wants to buy her."

Caroline lifted her shirt and flashed her titties. There were shouts and whistles. Alaric came to see what was going on. "Caroline, put your shirt down!"

"It was Stefan's idea!" Caroline said, winking at Stefan.

"It wasn't my idea!" Stefan said.

"Shut up! We're trying to get detention, remember?" Caroline said.

"Oh, yeah, it was totally my idea," Stefan said.

"Detention, both of you!" Alaric yelled.

Caroline lead Stefan by the hand to the detention room. "Now that we're all alone..." She pulled her dress over her head leaving her in a black lace bra and a thong. She pushed him to the couch and danced for him.

"Am I supposed to put money in your underwear?" Stefan asked.

"Shh," Caroline whispered putting a finger to her lips. Then she unhooked her bra and let it fall to the floor. She put her thumbs in the waist of her panties and tugged them down. "Get naked."

Stefan got naked, wondering why he didn't feel anywhere near as excited as he did when he was with Klaus. Thinking of Klaus helped him get it up.

Stefan pulled a condom out of his jean pocket. "Let's be safe."

(**A/N: Always wear condoms when having sex, especially with hookers. That skank might have an infection.)**

He slid the condom on and entered Caroline. "Umm... is it in?" she asked uncertainly.

"Yes!" Stefan said exasperatedly.

Stefan started thrusting. "Oh yeah, baby that's so good," Caroline said in a monotone voice.

Stefan was thinking of Klaus so he came abruptly, yelling "Klaus!" as he did so.

"What?" Caroline said offended, knowing that Jeremy was probably listening outside the door. Then she whispered in Stefan's ear, "It's okay, I was thinking of Klaus, too."

Meanwhile in the men's washroom, Jeremy has put a closed for cleaning sign up so no one else would enter. "So how do we want to do this?" he asked.

"I was thinking we'd just wing it?" Tyler asked.

"Alright, everybody strip," Jeremy commanded.

Jeremy stripped like a pro. Bonnie awkwardly kicked off her hooker boots. Soon they were all naked. Jeremy pushed Bonnie up against a urinal and fucked her slowly. Tyler stood there awkwardly and watched.

"So are you going to join in or what?" Jeremy asked.

"Umm... yeah, sure," Tyler said. He pushed into Jeremy who soon forgot entirely about Bonnie who was left to stand at the sidelines, sad that no one wanted her.

Then Jeremy got bored and said, "Do her."

Tyler obliged, and he came at the same time Bonnie did.

"Can I put my fucking pants back on?" Jeremy asked.

"Umm, sure..." Tyler said.

"Where did you get ten thousand dollars anyway?" Bonnie asked.

* * *

Carol Lockwood opened her purse and was shocked to find it empty. "Where's my goddamn hooker money?"

* * *

**A/N: I think that clears up all the outstanding pairing requests. Please make more? Oh and I'm serious about the condoms guys. Cover your stump before you hump.**


	6. Two Mystery Pairings!

Jeremy had called all his hookers and informed them that it was payday. They met in Jeremy's office, AKA Stefan's bedroom. He told Damon, Bonnie, and Caroline to stand in a straight line.

"Bonnie Bennett," Jeremy said. "You have earned one Watermelon Ring Pop,"

"...Okay,'" Bonnie said sadly.

"Caroline Forbes," Jeremy continued. "You have earned one Cotton Candy Ring Pop."

Caroline smiled. She remembered that she had only earned Jeremy five cents, so she figured she was coming out ahead.

"Damon Salvatore," Jeremy said handing him a briefcase of money. "Ninety thousand dollars and a new pair of leather pants."

"Are you fucking serious?" Bonnie said. "All I got was a ring pop! I don't even like watermelon!"

"I'll trade you," Caroline said.

"No tradesies!" Jeremy said. "Now, it's time we upgrade our business. You ladies better start working harder if you ever want to earn the big bucks."

"How come I didn't get a Ring Pop?" Damon complained.

"I'm so sorry, Damon. How could I ever be so stupid? What flavor do you want?" Jeremy asked. Bonnie scowled.

"Blue-raspberry," Damon said.

"Here, have seven!" Jeremy said throwing them at him.

Damon picked up the scattered Ring Pops off the ground. "I'm just having the best day!"

* * *

Jeremy stood at the Mystic Grill, handing out pamphlets. They read_ Jeremy's Pimp Business. First class hookers Bonnie Bennett, Caroline Forbes, Damon Salvatore, and our new mystery hooker. Prices are negotiated on an individual basis._

Elijah grabbed a pamphlet. "I want the mystery whore."

"Excellent," Jeremy said. "That will be eighty-four dollars and seventy-nine cents."

"Can I just give you a hundred?' Elijah asked.

"I _guess_," Jeremy said. "She's in the women's washroom."

Elijah relieved that the mystery hooker was a women, smiled happily as he made his way to the bathroom. The stall door was closed, and all he could see was attractive feet in five inch black high heels. "Hi, I'm here for your services."

"Elijah?" the mystery whore asked.

"Yes. Who are you?" Elijah said.

"Elijah, I'm not coming out!" the girl cried.

"Why not?" Elijah asked.

"I'm Rebekah!"

"Rebekah, I already paid!" Elijah said.

"I need a twenty dollar tip," Rebekah bargained.

"Done," Elijah said. He pushed a twenty dollar bill under the bathroom door. Rebekah opened the door. She was wearing absolutely nothing but her heels.

"Come here, Sunshine," she said erotically.

Elijah immediately forgot that this was his sister and took off his clothes. He pinned her against the bathroom wall. They were the same height when Rebekah had her heels on, so it was easy for him to enter her.

"Aren't you at least going to give me a little lick before you get yours?" Rebekah asked.

"Fine," Elijah said dropping to his knees and licking her junk sexually.

"Mmm..." Rebekah cried. Elijah went down on her for twenty solid minutes before she came.

"Now is it my turn?" he asked.

"Sure," Rebekah said, panting.

Elijah inserted himself in her and rocked back and forth slowly.

"Can't you go a little faster?" Rebekah asked.

"I paid for an hour!" Elijah said.

"Ugh!" Rebekah exclaimed.

Three hours and seventeen minutes later, Jeremy entered the bathroom. "Took you long enough. That'll be an additional forty-seven dollars for going over."

Elijah handed him a fifty.

"Now, I have another customer to deal with," Jeremy said.

* * *

Jeremy made his way back to the Salvatore's house, where's Matt's mom was waiting. "I'm here to buy Damon," she said.

"Of course," Jeremy said. "That'll be... forty thousand for an hour."

Matt's mom wrote a check.

Jeremy knocked on Damon's door. "Damon, open up!"

"Jeremy I need to sleep at some point!" Damon said opening the door.

"I don't pay you to sleep," Jeremy said. "Unless it's with people." He slapped Damon a high five, which Damon accepted before realizing he was actually mad at Jeremy.

"Fine, but you'd better make it quick," Damon said. "Why hello, Matt's mom."

"Hi, Donnie," she said.

"Umm... my name is Damon."

"His name is Big D," Jeremy said. "Have fun, kids."

Jeremy waited outside the door, hearing cries of "Oh, Donnie!" and "That's not my name!" He couldn't help but wonder what it would be like to sleep with Damon himself. Then he shook that thought away. Damon was far too classy for him. Jeremy didn't have that kind of money.

* * *

**A/N: For those of you who are interested, Damon earned 92K, a thousand which went towards new leather pants and a thousand that Jeremy kept.**


	7. Annemy

**A/N: I am going to get to all of the pairings that have been suggested. I even have ideas for all of them. This story is going to have many chapters. :)**

* * *

Anna knocked on the Gilbert's door. Elena answered. "Jeremy's not here. He lives with Damon now or something," she said. Anna raised an eyebrow, but figured she wouldn't jump to conclusions. She made her way to the Salvatore whorehouse.

She walked in without bothering to knock, since she didn't need invited in.

"Now, Stefan, since you are our best customer I decided to bestow upon you the greatest honour," Jeremy said. Anna wondered what the hell he was talking about. What was he selling Stefan?

"Umm, thanks?" Stefan said.

"Your reward is one blue raspberry Ring Pop," Jeremy said handing Stefan a package.

"Awesome!" Stefan said excitedly, ripping the package open.

Then Damon and Stefan shouted together, "Team Salvatore, ring power!" Then they bumped Ring Pops. Unfortunately, they got stuck together because Damon's was sticky with spit.

"What the hell Stefan!" Damon exclaimed.

"It's your fault!" Stefan said as they both attempted to pull apart.

"This is not good at all," Jeremy said. "Stefan if you're going to be stuck to Damon, you're going to have to witness some pretty sick stuff."

"Some pretty sick stuff like what?" Stefan said nervously. "I mean, just regular sex right, nothing weird?"

"Well, I'm pretty sure Elena has a thing for strapping on and fucking him in the ass,"(**A/N: Foreshadowing at it's finest.) ** Jeremy said. "Klaus pretty much beat the crap out of him. And I mean if it were _me _buying Damon I would get him to give me a blowjob in the shower so I could shampoo and condition his hair."

"What?" Anna almost yelled.

"What?" Jeremy said defensively. "You don't think his hair actually looks that great without conditioner, do you?"

"You're not going to buy Damon though, right?" Stefan said hopefully.

"Hi, Anna! Did you come for the hoes?" Jeremy asked.

"You're not going to buy Damon, _right_?" Stefan asked scared.

"Are you crazy?" Jeremy said. "I don't have that kind of green."

"Good," Damon said, looking away from Jeremy.

"How do you not have that kind of money?" Stefan asked. "I gave you like 50 K, two days ago!"

"You gave him fifty grand?" Anna asked. "What the hell for?"

"To buy me," Damon said proudly.

"That's fucking sick!" Anna said. "You two are _brothers_."

"It wasn't like that!" Stefan whined. "I just bought him so he would crossdress."

"That's not weird at all," Anna commented.

"If you're here to buy Damon, you're going to have to let Stefan watch. It costs extra," Jeremy said.

"I didn't agree to that!" Stefan said.

"Don't worry, I'll give you another Ring Pop," Jeremy said soothingly.

"Damon, I want to buy Jeremy," Anna said.

"That's not how it works!" Stefan complained. "Jeremy is the pimp, _Damon_ is the _hooker_."

"Depends on the price," Jeremy said casually.

"Jeremy, you're going to prostitute yourself?" Damon asked shocked. "I thought you were better than that."

"So it's okay if you do it, but if I do it it's horrible?" Jeremy asked. "Is this because I'm a girl?"

"Jeremy, you're not a girl," Anna said.

"I am in bed!" Jeremy said.

"On second thought, maybe I'm not interested..." Anna said.

"No, it's fine. I can be a man for a price," Jeremy said. "Thirty-five big ones."

"Thirty-five grand?" Anna asked pulling out her check book.

"No, I said thirty-five ones," Jeremy said.

"Seriously?" Damon asked. "I get like 20K for an hour, and you're charging thirty-five dollars?"

"Sounds fair," Stefan said.

Anna handed Jeremy thirty-five one dollar bills. Jeremy promptly handed them to Damon. "You're an excellent pimp, Damon."

"I didn't even do anything!" Damon said. "And if I was pimping you out, which I _wouldn't_, I would have charged a hell of a lot more than that."

"Shh," Jeremy said putting a finger to Damon's lip. "You be quiet now."

"Anyway, I paid, you have to put out now," Anna said.

"Let me lead you to my office," Jeremy said formally.

"Not my bedroom!" Stefan said. He went to chase after Jeremy but he couldn't because Damon was walking in the opposite direction.

"What are you some kind of pervert that wants to watch?" Damon said angrily.

"What do you have a problem with watching other people have sex?" Stefan asked.

"I don't want to watch Jeremy have sex!" Damon said.

"Neither do I..." Stefan said with shifty eyes.

* * *

In Jeremy's office Anna had just ripped off her dress to reveal nothing underneath.

"You know you have to wear that out of here, right?" Jeremy said.

"Don't you have some old clothes I could borrow?" Anna asked.

"Damon's clothes are for sale, but they don't come cheap. They smell like him, you know. People pay a lot for that," Jeremy said.

"Fine!"

"$2000 for pants, $1000 for a shirt. Underwear is extra. His panties are $10,000. I'll give you his bra for $5, but you have a bigger cup size than him."

"No shit, I have a bigger cup size than him! And I just won't wear panties then!" Anna said.

"Your loss," Jeremy said.

"Can you please just shut up and screw me?" Anna said, full of frustration. _Sexual_ frustration.

Jeremy stripped off his clothes, which were actually a v-neck and jeans that Damon had worn the day before. Then he went to Stefan's closet, which was full to the roof with condoms and sex toys. "What can I interest you in?" he asked.

"Just a condom," Anna said, lying on the bed, spreading her legs.

"You don't even want to do it on my desk?" Jeremy asked.

"No, just fuck me already!" Anna said.

Jeremy fucked her and she liked it.

* * *

**A/N: I feel like such a d-bag ending the chapter like that but oh, well. Don't mind my aggressively implying that Damon and Jeremy are in love. And aggressively being pro-condom. And aggressively liking the word aggressively.**

**The next chapter will be Katherine/Elena/Damon. I will try to post it later tonight.**


	8. Datherelena

**A/N: I have been asked if this story will contain actual smut. I have a hard time writing smut, but I plan to have some smutty chapters. Hopefully this one will be smutty enough. Also, I've been asked what PIMP stands for. It's like the 50 Cent song, it doesn't stand for anything it's just pimp.**

* * *

Katherine made her way to _Jugs_, a popular strip club in Mystic Falls. When she got there, the first thing that caught her eye was Elena, grinding a pole, wearing nothing but red lace panties.

"Hey, slut!" Katherine yelled.

"What? I'm working!" Elena said, not stopping dancing.

"Those are my panties!" Katherine said. "I thought you said you gave them back a month ago."

"Sorry," Elena says removing the panties, which were stuffed with ones. "Keep the money for you troubles."

"I can't believe you're a stripper," Katherine mused.

"Well, it's better than Damon!" Elena said defensively. "He's a whore now."

"Damon's a whore?" Katherine said interestedly. "And could we buy him with this kind of cash?"

"Maybe," Elena said doubtfully. "Why don't you just buy him yourself?"

"Shh," Katherine said. "You're going to go in on this."

"Okay, I got nothing better to do anyway," Elena said leaving the strip club without bothering to put her clothes back on.

* * *

"No, Katherine thought I was hotter!" Damon yelled at Stefan.

"That's preposterous!" Stefan yelled.

"Ladies, ladies," Jeremy said. "We all know that if Katherine had half a brain she would think Damon was hotter."

"Ha!" Damon said.

Stefan tried to leave, but his Ring Pop was still stuck to Damon's and he was not willing to let go of that tasty blue raspberry flavour.

Katherine and Elena walked in. "Jeremy!" Elena said. "We require Damon's services."

Katherine just smiled and said, "Eleanor and I are going to have a threesome."

"Eleanor?" Jeremy asked. "That is one shitty stripper name."

"It's my classy bitch name!' Eleanor said slapping him.

"Oh," Jeremy said. "In that case it suits you."

"How much?" Katherine asked, pulling out her check book. "We're going to have a tea party first so we probably need three hours."

"A hundred grand," Jeremy said. "Each."

"Jeremy, I'm your sister!" Eleanor said.

"Fine, a hundred for Katherine, fifty for you," Jeremy said.

Katherine wrote him a check for a hundred and fifty grand, paying Eleanor's share.

"Katherine, who's hotter me or Damon?" Stefan asked.

"Damon," Katherine said without thinking.

"Dammit!" Stefan said.

"Oh, and Stefan has to watch, he's currently attached to Damon," Jeremy pointed out.

"Like at the hip?" Katherine asked.

"No, at the Ring Pop," Damon said sassily.

"Excellent," Eleanor said. "I like it when people watch."

* * *

Ten minutes later, the foursome was sitting in Damon's room. Katherine and Eleanor had set up a short table and three stools, one for each of them and one for Damon. Stefan sat awkwardly on the floor.

"Here, have some tea," Katherine said.

"...Okay," Damon said. He had been asked to do a lot worse things. He took a sip and spit it right back out. "This is vervain!"

"Drink it!" Eleanor said slapping him in the back of the head.

"Would you like some tea, Stefan?" Katherine asked.

"No, thank you..." Stefan said.

"Okay, this tea party is boring let's get to the sex," Eleanor said.

Katherine throw Damon (and consequently Stefan) against the tea party table. Her tea spilt. Katherine slapped Damon across the face. "How dare you spill my tea?"

"I didn't do anything!" Damon yelled.

"Get naked!" Eleanor yelled.

Damon awkwardly stripped, having to get Stefan to help him.

Eleanor, of course was already naked. Katherine unzipped her dress and took off the red lace panties Elena had borrowed.

Katherine ran her hands through Eleanor's straight hair and kissed her savouring the warmth of their mouths together.

"I could get used to this!" Damon said.

"Am I allowed to take my clothes off?" Stefan asked.

"No!" Eleanor and Katherine said at the same time.

"Fine," Stefan said, brooding.

Katherine got down on her knees and spread the outer lips of Eleanor's vulva, and drank in the taste of her sweet juices. Eleanor pulled Katherine's hair and moaned.

"Wait," Eleanor said suddenly. "I thought we were paying to have sex with Damon."

"No, no," Damon said. "That's fine, carry on doing what you're doing."

"Elena, if you ever loved me, you'll let me join in on this," Stefan said.

"Quiet!" Katherine said kicking Stefan in the face. Stefan didn't mind though because it gave him a great view of her vagina. "So I was thinking Damon fucks you, while you go down on me."

"That sounds reasonable," Damon said. Stefan slapped him.

"Sure," Eleanor said hopping on Damon's cock.

"Wait!" Jeremy said entering the room.

"Jeremy get out!" Eleanor said, throwing a full teacup at him.

"You forgot the condom you slut!" Jeremy said, throwing condoms everywhere.

"Fine!" Eleanor said angrily ripping open a package and sliding a condom on Damon.

"Am I allowed to move or is this going to be like last time?" Damon asked.

"What happened last time?" Stefan said.

"She whipped me and told me to shut up the whole time," Damon said.

"Yeah, she does that," Stefan said, pretending he had slept with Elena. Which he hadn't.

"Don't move." Elena proceeded to ride Damon cowgirl style. Katherine then stood on the table and grinded her hips against Elena's face, as Elena gently nibbled on her clit.

Damon came immediately and for some reason that he didn't answer he yelled out "Jeremy!"

"What the fuck?" Eleanor said.

Jeremy, who had been waiting outside the door the whole time walked in. "What is it Damon?"

"Nothing..." Damon said awkwardly.

"Jeremy this is ridiculous," Eleanor said. "We didn't pay a hundred and fifty thousand dollars to have Damon last thirty seconds."

"That's hardly my fault!" Jeremy said. "Come on Damon, you're better than that!" He slapped Damon on the back of the head. This caused Damon to flail his Ring Pop hand into Stefan's face.

"Aww man, it's stuck to my face!" Stefan said.

"You know what both of you just get out of here and leave Eleanor and I alone!" Katherine said angstily.

Damon and Stefan walked out and closed the door. Jeremy stayed there listening against the door.

"So you just listen every time someone has sex?" Damon asked.

"I've got to make sure my customers are satisfied!" Jeremy said.

"Katherine, what the hell?" Eleanor yelled. "Actually, wait that's kind of good..."

"On second thought, maybe I don't want to hear this," Jeremy said. "Let's go get ice cream."

* * *

**A/N: I'm sorry this took so long to update. I'm also sorry it's not smutty. I tried, I honestly did. This chapter was really hard to write though. Anyway, hope you liked it!**


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